Literature DB >> 28911772

Kinetic Deuterium Isotope Effects in Cytochrome P450 Reactions.

Frederick P Guengerich1.   

Abstract

Cytochrome P450 (P450, CYP) research provides many opportunities for the application of n class="Disease">kinetic isotope effect (KIE) strategies. P450s collectively catalyze oxidations of more substrates than any other group of enzymes, and CH bond cleavage is a major feature in a large fraction of these reactions. The presence of a significant primary deuterium KIE is evidence that hydrogen abstraction is at least partially rate-limiting in the reactions, and this appears to be the case in many P450 reactions. The first report of a KIE in (P450-linked) drug metabolism appeared in 1961 (for morphine N-demethylation), and in a number of cases, it has been possible to modulate the in vivo metabolism or toxicity of chemicals by deuterium substitution. A number of efforts are in progress to utilize deuterium substitution to alter the metabolism of drugs in an advantageous manner.
© 2017 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  Cytochrome P450; Deuterium; Drug development; Drug metabolism; Hydroxylation; Intrinsic isotope effect; Kinetic isotope effects

Mesh:

Substances:

Year:  2017        PMID: 28911772      PMCID: PMC5776663          DOI: 10.1016/bs.mie.2017.06.036

Source DB:  PubMed          Journal:  Methods Enzymol        ISSN: 0076-6879            Impact factor:   1.600


  67 in total

1.  Stereochemical dynamics of aliphatic hydroxylation by cytochrome P-450.

Authors:  R E White; J P Miller; L V Favreau; A Bhattacharyya
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

2.  Metabolic studies with deuterated phenobarbital.

Authors:  J M Perel; P G Dayton; C L Tauriello; L Brand; L C Mark
Journal:  J Med Chem       Date:  1967-05-01       Impact factor: 7.446

3.  Effect of deuteration of the O-CH3 group on the enzymic demethylation of o-nitroanisole.

Authors:  C Mitoma; D M Yasuda; J Tagg; M Tanabe
Journal:  Biochim Biophys Acta       Date:  1967-04-25

4.  Deuterium isotope effects on the metabolism and toxicity of phenacetin in hamsters.

Authors:  S D Nelson; W A Garland; J R Mitchell; Y Vaishnav; C N Statham; A R Buckpitt
Journal:  Drug Metab Dispos       Date:  1978 Jul-Aug       Impact factor: 3.922

5.  In vitro metabolic studies on propyl p-nitrophenyl ether.

Authors:  C Mitoma; R L Dehn; M Tanabe
Journal:  Biochim Biophys Acta       Date:  1971-04-20

6.  Deuterium and tritium kinetic isotope effects on initial rates.

Authors:  D B Northrop
Journal:  Methods Enzymol       Date:  1982       Impact factor: 1.600

7.  Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate.

Authors:  J T Groves; G A McClusky
Journal:  Biochem Biophys Res Commun       Date:  1978-03-15       Impact factor: 3.575

8.  Oxidative cleavage of carboxylic esters by cytochrome P-450.

Authors:  F P Guengerich
Journal:  J Biol Chem       Date:  1987-06-25       Impact factor: 5.157

9.  Effect of deuteration of N--CH3 group on potency and enzymatic N-demethylation of morphine.

Authors:  C ELISON; H RAPOPORT; R LAURSEN; H W ELLIOTT
Journal:  Science       Date:  1961-10-13       Impact factor: 47.728

10.  Mechanism of the third oxidative step in the conversion of androgens to estrogens by cytochrome P450 19A1 steroid aromatase.

Authors:  Francis K Yoshimoto; F Peter Guengerich
Journal:  J Am Chem Soc       Date:  2014-10-10       Impact factor: 15.419

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  10 in total

Review 1.  Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.

Authors:  F Peter Guengerich; Francis K Yoshimoto
Journal:  Chem Rev       Date:  2018-06-22       Impact factor: 60.622

2.  Mechanism-Guided Design and Discovery of Efficient Cytochrome P450-Derived C-H Amination Biocatalysts.

Authors:  Viktoria Steck; Joshua N Kolev; Xinkun Ren; Rudi Fasan
Journal:  J Am Chem Soc       Date:  2020-06-01       Impact factor: 15.419

3.  Stable isotope-labelled morphine to study in vivo central and peripheral morphine glucuronidation and brain transport in tolerant mice.

Authors:  Ivan Weinsanto; Alexis Laux-Biehlmann; Jinane Mouheiche; Tando Maduna; François Delalande; Virginie Chavant; Florian Gabel; Pascal Darbon; Alexandre Charlet; Pierrick Poisbeau; Marc Lamshöft; Alain Van Dorsselaer; Sarah Cianferani; Marie-Odile Parat; Yannick Goumon
Journal:  Br J Pharmacol       Date:  2018-08-31       Impact factor: 8.739

4.  Methylene Oxidation of Alkyl Sulfates by Cytochrome P450BM-3 and a Role for Conformational Selection in Substrate Recognition.

Authors:  F Peter Guengerich; Mostafa I Fekry
Journal:  ACS Catal       Date:  2020-04-02       Impact factor: 13.084

5.  A Modified Arrhenius Approach to Thermodynamically Study Regioselectivity in Cytochrome P450-Catalyzed Substrate Conversion.

Authors:  Rosa A Luirink; Marlies C A Verkade-Vreeker; Jan N M Commandeur; Daan P Geerke
Journal:  Chembiochem       Date:  2020-02-25       Impact factor: 3.164

6.  Production of Deuterated Cyanidin 3-O-Glucoside from Recombinant Escherichia coli.

Authors:  Mamta Gupta; Jian Zha; Xing Zhang; Gyoo Yeol Jung; Robert J Linhardt; Mattheos A G Koffas
Journal:  ACS Omega       Date:  2018-09-24

7.  Structure-Guided In Vitro to In Vivo Pharmacokinetic Optimization of Propargyl-Linked Antifolates.

Authors:  M N Lombardo; N G-Dayanandan; S Keshipeddy; W Zhou; D Si; S M Reeve; J Alverson; P Barney; L Walker; J Hoody; N D Priestley; R S Obach; D L Wright
Journal:  Drug Metab Dispos       Date:  2019-06-14       Impact factor: 3.922

Review 8.  Cytochrome P450 2E1 and its roles in disease.

Authors:  F Peter Guengerich
Journal:  Chem Biol Interact       Date:  2020-03-18       Impact factor: 5.192

9.  A New Highly Deuterated [18F]AV-45, [18F]D15FSP, for Imaging β-Amyloid Plaques in the Brain.

Authors:  Hao Xiao; Seok Rye Choi; Ruiyue Zhao; Karl Ploessl; David Alexoff; Lin Zhu; Zhihao Zha; Hank F Kung
Journal:  ACS Med Chem Lett       Date:  2021-06-21       Impact factor: 4.632

10.  Twelfth-Position Deuteration of Nevirapine Reduces 12-Hydroxy-Nevirapine Formation and Nevirapine-Induced Hepatocyte Death.

Authors:  Carley J S Heck; Herana Kamal Seneviratne; Namandjé N Bumpus
Journal:  J Med Chem       Date:  2020-02-27       Impact factor: 7.446

  10 in total

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